153 Old Sherman Hill Road

Woodbury, CT
$ 599,900 Beds 3 Baths 1.5 Sq 1,658
Monthly Estimate* How much can I afford?

Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper level includes 3 bedrooms, a full bath, and access to a walk-up attic from the primary bedroom. The main level offers a half bath and a functional, open layout. Additional property highlights include a separate 962 sq. ft., 2-bedroom guest house-offering incredible potential for an in-law suite or rental income once renovated (appears to be separately metered). The property also features two massive, 2-story barns that appear to have electricity. Tremendous upside potential for an end-user, investor, or multi-generational living. Subject to probate approval. Property sold as-is; no disclosures.

Single Family

  • Price
  • $ 599,900
  • City
  • Woodbury
  • Bedrooms
  • 3
  • Full Bathrooms
  • 1
  • County
  • Litchfield
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 3.51 Acres
  • Zip
  • 06798
  • Sqr Footage
  • 1,658
  • Year Built
  • 1903
  • Taxes
  • $ 7896
  • Style
  • MLS#
  • 24194640
Listed By: Heather Weber 203-232-5483 with Coldwell Banker Realty. - (203) 888-1845
Data Source: Smart MLS

Features

General

Zoning OS60
Neighborhood Sherman Hill
County Litchfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 3.51
Directions Corner of Sage and Old Sherman Hill.
High School Per Board of Ed
City Woodbury
Elementary School Per Board of Ed
Sq Ft Total 1658
DOM 25
Year Built 1903
Style Colonial,Victorian
Year Built Source Public Records

Interior Features

Cooling System None
Total Rooms 7
Basement Description Full,Unfinished

Exterior Features

Water Source Private Well
Lot Description Lightly Wooded,Level Lot,Open Lot

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Per Board of Ed Elementary School
Middle School Unknown Middle School
High School Per Board of Ed High School

Price History

8/10/2026 Listed $750,000
8/17/2026 7% - $699,900
9/4/2026 14% - $599,900

Property vs Zip Code Average in 06798

Price
AVG $880K
$600K
Taxes
AVG $8,969
$7,896
Year Built
AVG 1923
1903

153 Old Sherman Hill Road Woodbury, CT is a Single Family Home for sale at $599900 with 1658 sqft and a lot size of 3.51 Acres Acre(s). 153 Old Sherman Hill Road Woodbury has 3 bedrooms, 1 baths and was built in 1903. The property's zip code is 06798 which is in Woodbury, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.